Methanol → 5,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronaphthalene

HRID 1060703

Reaktionsgleichung

Reaktionsgleichung von HRID 1060703
Br[C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[C:5]([Br:10])=[C:4]([CH3:11])[C:3]=1Br.[O:13]1C=[CH:16][CH:15]=[CH:14]1.[Li][CH2:19]CCC.CO>C1(C)C=CC=CC=1.O>[Br:10][C:5]1[C:6]([Br:9])=[C:7]([CH3:8])[CH:2]=[C:3]2[C:4]=1[C:11]1([CH3:19])[O:13][CH:14]2[CH:15]=[CH:16]1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8029FuranHCID 31952Benzene, 1,2,4,5-tetrabromo-3,6-dimethyl-HCID 178418339Butyllithium

Produkt 1

HCID 226789125,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronaphthaleneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values.22

Aufarbeitung

  1. temperatureto warm to rt
  2. waitAfter 3 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with Et2O
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fd02ffed20e44a959ccb4cdc5ae1fffe
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525068B1

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